The mechanical properties and anatomy of fruit wall peels and their enzyme-isolated cuticular membranes (CM) are reported for three cherry tomato (Lycopersicon esculentum Mill.) cultivars that are crack-resistant, crack-intermediate, and crack-prone (i.e., Inbred 10, Sweet 100, and Sausalito Cocktail, respectively). The resistant and intermediate fruit peels strain-hardened when extended progressively; those of the crack-prone cultivar did so only modestly. The CM of all cultivars strain-hardened when extended with small forces; the CM of the intermediate and crack-prone cultivars strain-softened under tensile forces that did not strain-soften the crack-resistant cultivar. The peels and CM of the resistant cultivar were stiffer, stronger, and required more energy to break than crack-prone peels. The CM of crack-resistant peels developed deeper within the subepidermis than in the crack-prone or crack-intermediate peels. The CM in the outer epidermal periclinal walls of the crack-resistant and crack-intermediate cultivars was thicker than that of crack-prone peels. These data indicate that CM thickness can be used to gauge crack susceptibility among cherry tomato fruit, which can be useful in breeding programs and would facilitate QTL mapping of the underlying genetic factors.